#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/65/7106513.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7106513
loop_
_publ_author_name
'Shengcai Zheng'
'Weiwing Huang'
'Ning Gao'
'Ruimin Cui'
'Min Zhang'
'Xiaoming Zhao'
_publ_section_title
;
 One Pot Iridium-Catalyzed Asymmetrical Double Allylations of Sodium
 Sulfide:a Fast and Economic Way to Construct Chiral C2-Symmetric
 Bis(1-Substituted-Allyl)Sulfane
;
_journal_name_full               Chem.Commun.
_journal_page_first              6969
_journal_paper_doi               10.1039/c1cc11930c
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C18 H16 Br2 O2 S'
_chemical_formula_weight         456.19
_chemical_melting_point          148.6(10)
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.096(10)
_cell_angle_beta                 90.099(12)
_cell_angle_gamma                90.035(12)
_cell_formula_units_Z            2
_cell_length_a                   6.941(6)
_cell_length_b                   7.130(6)
_cell_length_c                   18.450(15)
_cell_measurement_temperature    293(2)
_cell_volume                     913.1(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.903
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4462
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    4.560
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.800
_refine_diff_density_min         -1.459
_refine_diff_density_rms         0.148
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.49(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         4462
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0775
_refine_ls_shift/su_max          0.090
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1778P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2218
_refine_ls_wR_factor_ref         0.2412
_reflns_number_gt                3347
_reflns_number_total             4462
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc11930c.txt
_cod_data_source_block           xl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '147.6-149.5' was changed to
'148.6(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1673 2011-04-08 12:14:43Z adriana 
;
_cod_original_cell_volume        913.0(13)
_cod_original_sg_symbol_H-M      P1
_cod_database_code               7106513
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.6980(2) 2.1779(2) 0.25712(8) 0.0720(5) Uani 1 1 d . . .
Br2 Br 0.1982(2) 2.3244(2) -0.95381(8) 0.0723(5) Uani 1 1 d . . .
Br3 Br 0.6627(2) 2.3245(2) -0.24320(8) 0.0721(5) Uani 1 1 d . . .
Br4 Br 1.1627(2) 2.1776(2) -0.45392(8) 0.0719(5) Uani 1 1 d . . .
O1 O 0.583(3) 2.4920(18) -0.6238(7) 0.114(7) Uani 1 1 d . . .
O2 O 0.257(3) 2.4921(19) -0.5773(7) 0.107(6) Uani 1 1 d . . .
O3 O 0.759(3) 2.0055(19) -0.1216(7) 0.118(7) Uani 1 1 d . . .
O4 O 1.091(3) 2.0069(17) -0.0775(7) 0.102(5) Uani 1 1 d . . .
S1 S 0.4260(9) 2.5942(5) -0.5996(2) 0.0722(12) Uani 1 1 d . . .
S2 S 0.9239(9) 1.9022(6) -0.0997(2) 0.0737(13) Uani 1 1 d . . .
C1 C 0.5981(14) 2.4439(12) -0.3309(4) 0.053(3) Uani 1 1 d G . .
C2 C 0.4265(12) 2.5414(14) -0.3402(4) 0.054(3) Uani 1 1 d G . .
H2B H 0.3357 2.5438 -0.3032 0.065 Uiso 1 1 calc R . .
C3 C 0.3907(11) 2.6355(14) -0.4048(4) 0.061(4) Uani 1 1 d G . .
H3B H 0.2759 2.7008 -0.4110 0.073 Uiso 1 1 calc R . .
C4 C 0.5265(13) 2.6320(13) -0.4601(4) 0.049(3) Uani 1 1 d G . .
C5 C 0.6981(12) 2.5344(14) -0.4508(4) 0.061(4) Uani 1 1 d G . .
H5A H 0.7889 2.5321 -0.4878 0.074 Uiso 1 1 calc R . .
C6 C 0.7339(12) 2.4404(13) -0.3862(5) 0.065(4) Uani 1 1 d G . .
H6A H 0.8487 2.3751 -0.3800 0.078 Uiso 1 1 calc R . .
C7 C 0.4911(18) 2.7505(17) -0.5270(6) 0.047(3) Uani 1 1 d D . .
H7A H 0.3818 2.8339 -0.5175 0.056 Uiso 1 1 calc R . .
C8 C 0.662(2) 2.8684(17) -0.5476(9) 0.063(4) Uani 1 1 d D . .
H8A H 0.7765 2.8110 -0.5609 0.075 Uiso 1 1 calc R . .
C9 C 0.649(3) 3.0516(19) -0.5468(10) 0.076(5) Uani 1 1 d D . .
H9A H 0.5346 3.1093 -0.5335 0.091 Uiso 1 1 calc R . .
H9B H 0.7554 3.1240 -0.5596 0.091 Uiso 1 1 calc R . .
C10 C 0.3558(19) 2.7496(16) -0.6726(6) 0.048(3) Uani 1 1 d D . .
H10A H 0.4639 2.8341 -0.6826 0.058 Uiso 1 1 calc R . .
C11 C 0.186(2) 2.8666(16) -0.6494(8) 0.058(4) Uani 1 1 d D . .
H11A H 0.0734 2.8081 -0.6345 0.069 Uiso 1 1 calc R . .
C12 C 0.196(3) 3.0531(18) -0.6502(9) 0.073(5) Uani 1 1 d D . .
H12A H 0.3087 3.1122 -0.6652 0.088 Uiso 1 1 calc R . .
H12B H 0.0906 3.1241 -0.6358 0.088 Uiso 1 1 calc R . .
C13 C 0.3165(14) 2.6388(12) -0.7390(4) 0.053(3) Uani 1 1 d G . .
C14 C 0.4543(11) 2.6393(12) -0.7936(5) 0.057(3) Uani 1 1 d G . .
H14A H 0.5696 2.7037 -0.7870 0.069 Uiso 1 1 calc R . .
C15 C 0.4198(12) 2.5436(13) -0.8580(4) 0.052(3) Uani 1 1 d G . .
H15A H 0.5121 2.5440 -0.8945 0.063 Uiso 1 1 calc R . .
C16 C 0.2475(14) 2.4474(12) -0.8679(4) 0.053(3) Uani 1 1 d G . .
C17 C 0.1097(11) 2.4469(13) -0.8133(5) 0.067(4) Uani 1 1 d G . .
H17A H -0.0056 2.3826 -0.8199 0.080 Uiso 1 1 calc R . .
C18 C 0.1442(12) 2.5426(13) -0.7489(4) 0.058(4) Uani 1 1 d G . .
H18A H 0.0519 2.5423 -0.7124 0.069 Uiso 1 1 calc R . .
C19 C 1.1011(15) 2.0503(12) -0.3691(4) 0.054(3) Uani 1 1 d G . .
C20 C 0.9288(13) 1.9543(14) -0.3592(4) 0.063(4) Uani 1 1 d G . .
H20A H 0.8371 1.9523 -0.3960 0.075 Uiso 1 1 calc R . .
C21 C 0.8936(11) 1.8614(14) -0.2944(5) 0.060(4) Uani 1 1 d G . .
H21A H 0.7783 1.7972 -0.2878 0.072 Uiso 1 1 calc R . .
C22 C 1.0307(14) 1.8645(14) -0.2394(4) 0.052(3) Uani 1 1 d G . .
C23 C 1.2030(13) 1.9605(16) -0.2492(5) 0.076(6) Uani 1 1 d G . .
H23A H 1.2948 1.9626 -0.2125 0.091 Uiso 1 1 calc R . .
C24 C 1.2383(12) 2.0534(15) -0.3141(5) 0.067(4) Uani 1 1 d G . .
H24A H 1.3536 2.1176 -0.3206 0.080 Uiso 1 1 calc R . .
C25 C 0.993(2) 1.7434(18) -0.1713(7) 0.052(3) Uani 1 1 d D . .
H25A H 0.8841 1.6596 -0.1815 0.063 Uiso 1 1 calc R . .
C26 C 1.163(2) 1.626(2) -0.1480(9) 0.080(6) Uani 1 1 d D . .
H26A H 1.2767 1.6855 -0.1347 0.095 Uiso 1 1 calc R . .
C27 C 1.156(3) 1.441(2) -0.1457(10) 0.073(5) Uani 1 1 d D . .
H27A H 1.0432 1.3783 -0.1588 0.087 Uiso 1 1 calc R . .
H27B H 1.2633 1.3726 -0.1311 0.087 Uiso 1 1 calc R . .
C28 C 0.853(2) 1.7469(16) -0.0272(7) 0.049(3) Uani 1 1 d D . .
H28A H 0.9622 1.6643 -0.0171 0.059 Uiso 1 1 calc R . .
C29 C 0.684(2) 1.623(2) -0.0475(9) 0.074(6) Uani 1 1 d D . .
H29A H 0.5691 1.6815 -0.0605 0.089 Uiso 1 1 calc R . .
C30 C 0.689(3) 1.437(2) -0.0479(10) 0.068(4) Uani 1 1 d D . .
H30A H 0.8021 1.3752 -0.0352 0.082 Uiso 1 1 calc R . .
H30B H 0.5803 1.3692 -0.0609 0.082 Uiso 1 1 calc R . .
C31 C 0.8149(14) 1.8592(12) 0.0404(4) 0.051(3) Uani 1 1 d G . .
C32 C 0.6425(12) 1.9545(14) 0.0508(4) 0.070(5) Uani 1 1 d G . .
H32A H 0.5496 1.9554 0.0144 0.084 Uiso 1 1 calc R . .
C33 C 0.6088(11) 2.0486(14) 0.1156(5) 0.065(4) Uani 1 1 d G . .
H33A H 0.4934 2.1124 0.1225 0.077 Uiso 1 1 calc R . .
C34 C 0.7475(14) 2.0474(13) 0.1700(4) 0.053(3) Uani 1 1 d G . .
C35 C 0.9199(12) 1.9520(14) 0.1596(4) 0.067(4) Uani 1 1 d G . .
H35A H 1.0127 1.9512 0.1961 0.080 Uiso 1 1 calc R . .
C36 C 0.9536(11) 1.8580(13) 0.0948(5) 0.060(4) Uani 1 1 d G . .
H36A H 1.0690 1.7942 0.0879 0.072 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 117.9(10) . . ?
O1 S1 C7 111.7(9) . . ?
O2 S1 C7 107.7(7) . . ?
O1 S1 C10 107.1(7) . . ?
O2 S1 C10 107.6(8) . . ?
C7 S1 C10 104.0(6) . . ?
O3 S2 O4 117.5(10) . . ?
O3 S2 C25 109.4(8) . . ?
O4 S2 C25 108.5(9) . . ?
O3 S2 C28 107.9(9) . . ?
O4 S2 C28 109.2(7) . . ?
C25 S2 C28 103.4(6) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 Br3 122.4(5) . . ?
C6 C1 Br3 117.5(5) . . ?
C1 C2 C3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 C7 118.6(7) . . ?
C5 C4 C7 121.2(7) . . ?
C6 C5 C4 120.0 . . ?
C5 C6 C1 120.0 . . ?
C8 C7 C4 113.0(11) . . ?
C8 C7 S1 110.8(9) . . ?
C4 C7 S1 107.5(8) . . ?
C9 C8 C7 120.3(14) . . ?
C13 C10 C11 112.7(11) . . ?
C13 C10 S1 109.8(7) . . ?
C11 C10 S1 109.8(9) . . ?
C12 C11 C10 120.6(13) . . ?
C14 C13 C18 120.0 . . ?
C14 C13 C10 118.1(8) . . ?
C18 C13 C10 121.8(8) . . ?
C15 C14 C13 120.0 . . ?
C14 C15 C16 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 Br2 120.3(5) . . ?
C17 C16 Br2 119.6(5) . . ?
C18 C17 C16 120.0 . . ?
C17 C18 C13 120.0 . . ?
C20 C19 C24 120.0 . . ?
C20 C19 Br4 123.3(5) . . ?
C24 C19 Br4 116.7(5) . . ?
C19 C20 C21 120.0 . . ?
C20 C21 C22 120.0 . . ?
C23 C22 C21 120.0 . . ?
C23 C22 C25 121.9(8) . . ?
C21 C22 C25 117.9(8) . . ?
C22 C23 C24 120.0 . . ?
C23 C24 C19 120.0 . . ?
C26 C25 C22 114.1(11) . . ?
C26 C25 S2 110.4(10) . . ?
C22 C25 S2 106.8(8) . . ?
C27 C26 C25 122.4(14) . . ?
C31 C28 C29 112.2(11) . . ?
C31 C28 S2 109.7(7) . . ?
C29 C28 S2 112.8(10) . . ?
C30 C29 C28 124.2(14) . . ?
C32 C31 C36 120.0 . . ?
C32 C31 C28 121.7(7) . . ?
C36 C31 C28 118.3(7) . . ?
C31 C32 C33 120.0 . . ?
C34 C33 C32 120.0 . . ?
C35 C34 C33 120.0 . . ?
C35 C34 Br1 121.0(5) . . ?
C33 C34 Br1 119.0(5) . . ?
C34 C35 C36 120.0 . . ?
C35 C36 C31 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C34 1.888(7) . ?
Br2 C16 1.842(6) . ?
Br3 C1 1.884(6) . ?
Br4 C19 1.861(6) . ?
O1 S1 1.384(18) . ?
O2 S1 1.443(16) . ?
O3 S2 1.422(17) . ?
O4 S2 1.439(17) . ?
S1 C7 1.797(13) . ?
S1 C10 1.812(11) . ?
S2 C25 1.803(13) . ?
S2 C28 1.807(12) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C4 C7 1.518(13) . ?
C5 C6 1.3900 . ?
C7 C8 1.501(9) . ?
C8 C9 1.309(10) . ?
C10 C13 1.482(14) . ?
C10 C11 1.506(9) . ?
C11 C12 1.331(9) . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C19 C20 1.3900 . ?
C19 C24 1.3900 . ?
C20 C21 1.3900 . ?
C21 C22 1.3900 . ?
C22 C23 1.3900 . ?
C22 C25 1.548(13) . ?
C23 C24 1.3900 . ?
C25 C26 1.512(10) . ?
C26 C27 1.321(10) . ?
C28 C31 1.505(14) . ?
C28 C29 1.510(10) . ?
C29 C30 1.327(9) . ?
C31 C32 1.3900 . ?
C31 C36 1.3900 . ?
C32 C33 1.3900 . ?
C33 C34 1.3900 . ?
C34 C35 1.3900 . ?
C35 C36 1.3900 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139181946
